1-(2-bromobenzenesulfonyl)-2,4,5,6,7,7a-hexahydro-1H-indole | 1277155-96-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-bromobenzenesulfonyl)-2,4,5,6,7,7a-hexahydro-1H-indole
• 英文别名: 1-(2-bromophenyl)sulfonyl-2,4,5,6,7,7a-hexahydroindole
• CAS: 1277155-96-0
• 化学式: C₁₄H₁₆BrNO₂S
• 分子量: 342.257
• InChiKey: AJEIFHWPNHCHFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-bromobenzenesulfonyl)-2,4,5,6,7,7a-hexahydro-1H-indole 在 palladium diacetate 、 potassium carbonate 、 三苯基膦 、 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0~110.0 ℃ 、101.33 kPa 条件下， 反应 30.0h， 以62%的产率得到(4aRS,10aSR)-4a,10-ethano-2,3,4,4a,10,10a-hexahydro-1H-9-thia-10-azaphenanthrene 9,9-dioxide
  参考文献：
  名称：

  An Investigation into the One-Pot Heck Olefination−Hydrogenation Reaction

  摘要：

  Herein is described an operationally simple process concerning the observation that, following either inter-, or intramolecular Heck olefination, stirring of the so formed substituted alkenyl product under an atmosphere of hydrogen efficiently effects alkene hydrogenation. Overall this two-operation, one-pot "reductive Heck" sequence is notable since direct reductive Heck processes, using additives such as formate salts, are restricted to a limited range of substrates. In total 25 examples are reported (yields ranging from 0 to 95%), which were selected in order to probe the scope and limitations of this method. Finally, the utility of this sequence was demonstrated in a short synthesis of the calcimimetic agent, cinacalcet.

  DOI：

  10.1021/jo200023r